


All In Good Time

by DragonGirl420



Category: Supernatural
Genre: Dean Winchester Fluff, Dean Winchester Smut, F/M, SPN Dean Bingo, SPN Fluff Bingo, SPN Fluff Bingo 2019
Language: English
Status: Completed
Published: 2019-05-13
Updated: 2019-05-13
Packaged: 2020-03-02 18:08:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,356
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18816250
Author URL: https://archiveofourown.org/users/DragonGirl420/pseuds/DragonGirl420
Summary: Tired of seeing his best friend wallowing in whiskey after another disappointment, he finally confesses a well-kept secret.





	All In Good Time

**Author's Note:**

> A/N: Written for @spngenrebingo & @spndeanbingo. Please excuse the poorly written smut, it’s been a while since venturing down that path and I was constantly distracted but things OTHER than the smut at hand. Oh well, hope you enjoy it!
> 
> Square filled for SPN Genre Bingo: Best Friends to Lovers
> 
> Squared filled SPN Dean Bingo: FreeSpace

 

“Drinking that isn’t gonna make it stop, you know,” Dean said as he sat on the stool beside you.

“Stop what?” you asked without looking in his direction.

“Whatever you’re trying to forget.”

“You think you’re so damn smart, Winchester.” You did not need Dean’s brand of pep talk at the moment.

“Because I am,” he smirked. “As my best friend you should  _know_ how smart I am, and that I’m right about ninety-five percent of the time.” He finally turned to look at you and raised his brow teasingly. “If I remember correctly, last time you were throwing them back this hard, you’d been dumped by that chucklehead, Rocco. Can’t believe you dated a guy named Rocco…” he shook his head, disappointed in your past choices and drank his beer.

“Bite me,” you growled and threw back the rest of the whiskey in the glass.

You held it up for the bartender to refill and when he came to do so, Dean placed his hand over the top of the glass and slightly shook his head with a frown.  

“Dean, don’t be a dick—”

“She’s good,” he said to the bartender, who took one look at you and agreed that Dean was right.

“What the hell?! I wasn’t done,” you snapped at him, incredulous about his decision that you’d had enough to drink. “I’m not even that drunk!”

“Yeah, you are.” Dean slid the glass out of your reach, keeping his eyes locked with yours only infuriating you more.

“Who the  _fuck_  do you think you are? I’m a big girl, Dean. We aren’t fifteen anymore and you don’t need to protect me from myself or anyone else for that matter.”

 _WHO_  did he think he was, anyway? This night sucked. You got stood up for the second time by some guy you really thought could be the one. You thought he nearly perfect, and he seemed to accept your job and lifestyle as well as understood that you were a fiercely independent woman. Clearly, you’d been wrong and, so what, if you wanted to drink away the anger and hurt you felt for being duped, again.

“Me?” Dean mused, and sipped at his beer, “Oh, I’m just the guy who has been looking out for you for your whole damn life. The guy who knocked out Trent Moore when he tried to feel you up in the back of Bobby’s car. Also, the same guy who made sure that your shit-for-brains mother didn’t get you killed when she was drunk and went after a poltergeist.”

“Great, thanks for those reminders,” you moaned and turned on your stool to face the room and lean both elbows back on the bar. “Look, if you’re not gonna let me drink, lay off the trip down memory lane, okay? Not in the mood.”

“Deal.” Dean swallowed the rest of his beer and stood from the stool. “Come on then. W can shoot pool, or go watch a movie… whatever you want,” he reached out a hand to help you up, but you swatted him away.

“No! Just go, man. Let me wallow.”

“You know what… you’re a stubborn ass bitch. Fine, wallow! I’m so fucking tired of watching you do this. Oh, and next time you need a savior, sweetheart, call Sam, cause I’m done playing your white knight!”

Dean’s face was twisted in frustration, anger, and hurt, which left you confused. In all the years you had known him, he never got this mad at you before and you didn’t understand what made this time any different.

He reached into his pocket and slapped down cash on the bar, then turned and headed straight for the exit. You felt shocked and frozen in place, watching him storm through the bar and out the front door. Dean had been your best friend for most of your life, and sure there had been arguments; many, many arguments. But never had he straight up yelled at you before and it wasn’t sitting right to leave things with him like this.

You brushed your feelings of wallowing aside and found a purpose to move off the stool. The alcohol you’d already consumed made you feel lightheaded at the sudden movement, but your concern over Dean’s departure took precedence. No matter how you felt, you could not let him leave like that.

You found him in the parking lot. He was pacing back and forth in front of the Impala; his fists clenching and unclenching in sync with his jaw. You watched for a moment, hesitant to approach him in his current state. That’s when he looked up and saw you standing there. Unsure of what to say, you just shrugged. Your mouth fell open to speak but no words would come out.

Dean’s brow was still buried in frustration that was directed straight at you. It wasn’t like him to be this angry, not over you wanting to drink away the thoughts of another disappointment. Normally he joined in, helped you to bounce back by cracking jokes and getting drunk alongside you.

“I can’t with you right now, okay?” he grunted from under his breath. “Just go back inside.”

“Dean… I’m sorry. Whatever I said…”

He snorted a laugh and bite his lip. “You’re sorry. For what? You don’t even realize what you’re sorry for, do you?”

“No, I don’t. But clearly, I did  _something_  to piss you off. I never want to fight with you, Dean. Not  _really_  fight, anyway. So, whatever it was—”

“Fine, you wanna know? Really?” his voice rose with each word, his anger come through with each decibel.

Seeing him this way, and having it directed at you was not something you’d experienced before. Afraid that the wrong thing would make him angrier, all you could do was nod. Dean drew in a deep breath and closed his eyes. He was centering himself; he’d never admit that’s what he was doing, but it was. There was nothing you didn’t know about him. At least, you thought you knew everything about it.

“Since we were sixteen years old, any job we worked together, I watched you meet someone, hook up, and then get dumped. Each time, you ended up hurt, scared, or in a predicament that me or Sam had to rescue you from.”

His words stung and you wanted to be annoyed with him; but the truth was, Dean was right. There was nothing you could say that would help, so you remained silent and let him finish.

“For years, Y/N, years… We’ve worked together, killed some evil sons-of-bitches together… we’ve celebrated and mourned. We’ve drunk ourselves silly, and bandaged each other up, countless times…”

Dean paused, his entire body sighing as it released the built-up fury he had been holding onto. He unclenched his fists and took a few steps closer to where you stood.

“In all that time, I made some of the best memories of my life. Between you and Sam, you guys were my home. Everything good I can think of is wrapped up in you and my brother. So, you’ll have to excuse me if I am tired of seeing you get like that over yet another piece of shit asshole who can’t see how damn lucky he was that you even looked his way.”

You felt your stomach drop out, not because of what he said, but because of how he looked at you when he said it. Your mind flashed through a dozen scenarios where he had come to your rescue; with guys, monsters, your own mother and had even saved you from yourself a time or two. If it hadn’t been for Dean, you would have been dead years ago.

“I—I don’t know what to say other than, you’re right,” you said softly, the whiskey and culpability was still stinging in your throat. “I shouldn’t have depended on you for so long. I put you in these terrible situations, and—”

“Jesus Christ,” he muttered and brought his hand to his face, running it over his worn features. “You’re fucking clueless…”

“What now? I’m trying to apologize and tell you that you were right! What more do you want from me, Dean? What?!” You could feel your hands starting to shake, and a bubble of your rage starting to rise and your throat now on fire from the volume of your voice. “What the FUCK do you want from me, huh?!”

People passing by were starting to stare, so you closed the small bit of distance between you, ready to unload a little more without attracting a crowd. But when you got closer, Dean started to laugh.

“What the fuck is so funny?” you asked, breathing hard through your nose trying to simmer the boil of frustration.

“You. You look ridiculous when you get angry.” He was smiling now, not quite laughing, but the grin he wore was genuine and reserved for moments with people he trusted.

“You’re bipolar, Winchester,” you huffed, trying to contain your temperament.

Dean shrugged. “Maybe. But I think its more that you just drive me insane sometimes.”

“Oh sure, blame ME for  _your_  particular brand of crazy! I don’t know what to do any more here, man. I can’t do anything right with you, lately.”

“What the Hell does that mean?” Dean asked with a flare of insolence.

“The last three jobs we’ve worked? You barked at me for no reason. You’re short with me when I ask you to stop while on the road, you constantly ride me for shit that I have zero control over!”

“Then why do you stay, hm? Why not go off on your own? Hunt alone?”

“I’ve tried! You just keep finding me and taking me along to the next job! Friends don’t let friends hunt alone, remember?!”

Dean squeezed his eyes shut and drew in a deep breath. “I need a drink,” he said and pinched the bridge of his nose.

“Shouldn’t have closed out the bar tab,” you muttered.

“You know what—” he lifted his head, the look of aggravation back on his face. “I’m—this is—fuck it! God, you frustrate the  _shit out of me!_ ”

In a moment’s time, Dean had your face in his hands and his mouth on yours. Your first instinct was to retreat, then slap him across the face. Quickly following that, was the sudden desire to kiss him back. There had plenty of times you discreetly watched your best friend from the corner of your eye when he didn’t realize you were looking. How could you not? Dean was a gorgeous man, but more than that, he was sexy and funny. He was basically every girl’s fantasy. From his green eyes and freckles, right down to his bowlegs and boots. He was cocky and arrogant, smart as hell, and had a smile that could only be described as the devil’s handiwork. But never, in a million years, did you imagine he would have any interest in kissing you. In more than twenty years together, he never once tried nor looked at you like he wanted too; at least from what you could remember.

Dean’s lips were soft, yet he used them roughly against you. Every time you felt yourself pull back in the slightest, he continued to draw you in. You were fully immersed now, and when his mouth parted, you found yourself kissing him back just as greedily. His hand circled around to your neck and tangled up in your hair, entwining his fingers in the wispy strands and gripping them tightly. It caused a rush throughout your body; partially because of the whiskey still flowing through your veins, and partially because it just fucking felt so good.

You moaned softly into his mouth involuntarily and you felt his lips unfurl into a slight smirk. He slowly pulled away from your lips but left his hand concealed in your hair.

“Get in the car,” he growled. “ _Please_.” It was only to try and sound like he was being polite, but there was nothing well-mannered about the way he was holding you in his gaze. That’s when he released you completely, and there was no hesitation in your decision to get into the front seat of the Impala and leave with him.

Dean followed suit and got behind the wheel. He fired up the engine and before he put his most prized possession in gear, he reached out with his right hand and gripped your thigh. Sliding you closer to him, he kissed you again, gentle and wanting, leaving his hand to rest on your leg and kneading his fingers into your flesh as if he were a cat.

Without a word, he pulled back, put the car in gear, and speed off down the road to the motel you all had been staying at.

The motel door flew open with a bang. Dean pulled you into the room and slammed it shut so hard that it rebounded off the frame and opened again. You took a few more steps into the room he shared with Sam, though Sam was nowhere to be seen, and watched as Dean made sure the door was not only locked, but the chain was up.

You were almost afraid to speak. Dean had this look in his eyes that challenged you to say something, anything he could use to prove whatever point it was he was trying to make. But you didn’t give in. You were too nervous and excited about what was going to happen; realizing for the first time how  _much_  you had  _wanted_  it to.

He stalked you; his green eyes, now full of lust and want, were affixed to his prey. Dean moved slowly from the door to where you stood. As he crossed the room, he removed his jacket and threw it in the corner by the window. Next, his flannel came off and was tossed in the same direction. His eyes never wavering from you.

The ripple of his muscles on his arms was prominent now that his body was tense and anxious. The closer he got, the more your heart began to pound. How could you not have seen this in him before; all these years attached at the hip never once did you realize he would be looking at you the way he was then.

“I wasn’t gonna have this conversation with you in the parking lot of some dive bar,” he said, and despite the edge to his demeanor, his voice was gentle and calm. “I wasn’t gonna tell you, how many times I wanted to kill some guy who had his hands on you in some bar. Or a random joker on a case we were working, trying to get you meet them for drinks–”

“Dean…”

He ignored you. “I wasn’t going to tell you how many times I came so close to telling you that I wanted to be that guy and…” he trailed off, now directly in front of you, the arms you had just been admiring reaching out for you.

“And, what?” you managed to ask despite the lump in your throat.

Dean leaned in and kissed you again, slipping his arms around the lower part of your waist. When you felt him lift your feet off the ground, you let him and locked your arms around his neck. He took a few steps towards the bed and put you back on your feet at the foot of it.

“All those nights I watched you eyeing up any other guy but me… I was starting to resent you for it. Tonight, I finally realized that it’s my own damn fault.”

Your arms were still up around his neck, your lips a breath apart. “What do you mean?”

Dean didn’t answer at first, instead, he took your arms off his neck, and slipped your jacket off, letting it fall to the floor and kicking it out of the way.

“I got scared to tell you, that you were the one I wanted to take home every night. I should have told you. Instead, I kept quiet, would watch you go off with someone else and then I end up going home with some mediocre stand-in that never seemed to measure up to you.”

You didn’t know what to say. He hadn’t ever given you an indication he thought of you like that. Not that you had looked at the Winchesters as brothers, but there was a closeness that you felt to them; Dean especially. Anything physical felt like it would be crossing a line you couldn’t come back from. It was scary to think of life without Dean and Sam, and if you  _DID_  cross that line, it could go wrong and eventually cost you their place in your life? That couldn’t happen.

“Now you know why I wasn’t gonna let you wallow over some guy, not again. You can go if that’s what you want. Certainly not going to make you stay here, but I really want you too, Y/N. Stay tonight. Give this a chance.”

He was pleading with you now, nearly begging with the crease of his brow and the hope in his eyes. You couldn’t leave, you didn’t want too. He had been in front of you this entire time, and the only thing you wanted to forget was how many nights had been lost that you and he could have been together.

There weren’t any words that would convey what you wanted, so you took action instead. You locked in with his gaze and began to shed your layers of clothes until you stood before him in only your bra and underwear. His tongue ran nervously over his bottom lip at the sight of you while his eyes drank you in. Dean reached out and ran his fingers from your shoulder and down across your collarbone, then let them drift down your cleavage.

You took the bottom of his shirt, and pulled it up over his head, throwing it off to the side. From there, everything happened in what felt like seconds. Dean was kicking off his boots and pulling off his jeans. He had you down on the bed, laying his weight on top of you, running his hands across your flesh, and letting his mouth explore your neck. He pulled down your bra, exposing your breast to the warm air of the motel room. Dean brought his mouth to your nipple, running his tongue over it, making your entire body shiver.

His other hand ran down the length of your body, and pawed at the hem of your panties, yanking them down and finding the hood of your sex. Just the promise of his touch, caused his name to moan from your lips.

“Say it again,” he growled lowly, moving his mouth back up to your neck.

“ _Dean_ ,  _please…”_

His fingers slipped down and moved against your clit, the sensation of which was overwhelming. He moved slowly, toying with it, and with each pass against your most sensitive place, caused your back to arch up into him, and him to smile with satisfaction.

Dean moved further down, and let his fingers easily slid up into you, and the more you reacted to his touch, the more his erection grew against your leg. You dug your nails into his back, then ran them down to the boxers he still wore. Yanking them down, he looked down at you and smiled.

“Look who’s all impatient now,” he teased.

“Fuck you, Winchester,” you moaned as he thrust his fingers up into you with a bit more force making you gasp with both surprise and pleasure.

“In a minute, honey, in a minute… waited a long time for this…”

Before you could respond, Dean kissed you, hard. His tongue taking control and swirling with yours greedily. It was all too much for your overstimulated body, and you felt yourself ready to cum. Dean knew it too, he could feel the fluttering warmth of you around his hand, and it only made him insistent to continue.

You forced your head back, arching your chest up to him and cursed as he suddenly pulled his hand from you, before your release could come to fruition. He stood from the bed and let his boxers fall to the floor, before going into his jeans pocket, retrieving his wallet and pulling out the condom he kept there.

You sat up on your elbows and watched him curiously. “Look who’s mister responsibility,” you teased.

Dean shrugged but flashed that damn smirk. “Told you, been waiting for this for a long time. No way I was going to come unprepared.”

While he was taking care of the necessities, you moved further back on the bed after slipping off your bra and underwear. Dean finally climbed on the bed next to you; your heart pounding and your sex throbbing for more of him. You moved him so he was sitting against the headboard, and you straddled his lap, positioning yourself over him.

Dean’s gaze was greedy, but the animalistic lust he had earlier was gone; now he just watched you close, as if burning the memory of this night into his memory forever. As you sank down, letting his cock slide up into you, Dean’s eyes fluttered closed as his head rolled back against the headboard and his fingertips dug into your hips. It took only a second for you to start rocking against him; moving your hips in slow, methodical circles. With each pass, his mouth fell open, and his breathing intensified.

“Jesus…  _Fuuuuck_ …” he growled when you ran your nail up his chest and clasped your fingers behind his neck.

You guided his head to your chest, where he took your breast in his mouth, licking and sucking at your nipple. The faster you moved, the hungrier he became. Your head rolled back, and your overstimulated clit was pulsating with each pass you made against him. Your mind was completely lost in the moment with him; nothing before him had ever felt this good, this right… this euphoric.

His hands were beginning to grip you harder, moving you faster while his eyes opened and locked with yours. You wanted to speak, encourage him to fuck you as hard and fast as he wanted, but you didn’t have to because he saw it on your face. Your climax was rising again, and when you finally came, he did too, moaning your name and burying his head between your breasts. You could feel him throbbing inside you, matching his release with yours. Then, sighing as both of your muscles relaxed and you melted into each other.

A thin sheen of sweat coated both your bodies, as you cradled him against you. No rush to move off him, nor did he want that either. Dean lifted his head and reached his lips up to yours, as his hands slid around your waist and down over your ass.

“Worth the wait?” you asked, nearly breathless but smiling down at him.

Dean chuckled and moved his one hand up to brush a patch of sweaty hair from your brow. “And then some.”

You kissed him gently, then moved off his lap, falling to the bed beside him with a sigh of satisfaction. Dean reluctantly got up from the bed and excused himself to the bathroom. He was only gone a minute and leaped back into the bed next to you, attacking your neck with his mouth. Though you were exhausted, your body was still reeling from being with him. Forget the physical sensation, but the emotional one was all your mind could focus on now.

Dean Winchester, he had been your best friend for more than twenty years. He was the one you sought out for advice, he was your hunting partner, your drinking buddy, your partner in crime and in shenanigans. Now, was he really going to be your lover, too? Could you see yourself being with him like that? Risking a lifetime of friendship for the possibility of falling in love?

You wanted to say something, but not ruin the moment either. Instead, you just let yourself go, and tried not to think about it. Dean had the covers pulled up over you now, and rolled you onto your back while trailing light kisses along your shoulder.

“You okay with all this?” he asked, his expression turning serious.

“If you’re asking if I regret it, no, I don’t. But what is  _all this_ , exactly?”

“Whatever we want it to be. There’s no rules here, Y/N. You know, besides my brother, you’re the most important person in the world to me. And, yeah… I’ve wanted you for a long ass time. But I don’t want you to feel pressured.”

“Pressured into what?”

Dean considered for a moment and tried to choose his words carefully. “Being with me. Just me. If that’s not something you want—”

“Shut up,” you interrupted and sat up on one elbow. “I’m good right here with you, Dean. Doesn’t need to be defined. I realize now all those others were just a placeholder for you, too.”

“You really mean that?”

You nodded and kissed him. “Really.”

Dean settled back into the bed and drew you into the crook of his shoulder. You laid there wrapped in his arms, just breathing him in and relishing in this sudden turn life had taken when you heard the door start to open. The chain caught it and you pulled the covers up to your neck just as Sam’s face stuck through the crack in the door.

“Dean! Come on man, let me in,” he whined.

Dean looked to you and chuckled when he saw your expression. “You good?”

You nodded slightly and sunk down into the bed, pulling the covers over your head. You barely had time to register that you and Dean just had mind-blowing sex and were now discussing being a  _thing_ , but you had to contend with Sam, too?

“One minute,” he called out, and Sam shut the door.

Dean grabbed his boxers and jeans, slipped them back on and went to let his little brother in.

“Sorry, I was uh… entertaining,” Dean smirked and raised his eyes brows in triumph as Sam walked into the room.

“Man, seriously? Can’t you get your own room for that?”

“Sorry little brother, these things can’t be helped.”

Sam looked around and saw the mess of clothes all over the floor, then noticed your breathing lump beneath the covers.

“Dean,” he said through gritted teeth. “Your company is still here.”

“She sure is.”

“Hi Sam,” you spoke up sheepishly through the blanket over your face. “How’s it going?”

“Y/N?!” he gasped, his eyes wide with shock as he whipped his head around to look at his brother, who nodded still wearing his victorious smile. “Jesus…” Sam sighed and shook his head. “Well, damn, its about damn time. Geez. I just don’t get why you guys couldn’t have went to her room?”

“What?” you asked, sitting up and uncovering your face. “What does that mean…  _about time_?”

Sam’s face immediately blushed when he realized you were completely naked under the sheets. He turned his head and stuttered his response. “It’s—it—it’s just that… you and Dean, this has been coming for a while and—” he smacked himself in the head for his choice of words. “Dammit. You know what I mean. You know what, I’m gonna go… I can’t be here right now.”

“Take my room, Sam. Key is in my jacket pocket. And don’t worry, this doesn’t change anything. I promise I’ll still let you ride shotgun.”

Sam rolled his eyes, then quickly turned to grab your coat from the floor and retrieved the key before he made a quick exit from the room. Dean was snickering at his brother as he slammed the door behind him and could be seen nearly sprinting away down the walkway towards your room.

“So, that just happened,” you groaned and fell back to the bed.

“I wouldn’t worry about Sammy, he’ll take it all in stride.” Dean came back and laid down on top of the covers next to you. “Like he said, it’s been coming for a while.”

“In your mind, maybe,” you said quietly and cast your eyes away from his scrutiny. “I never thought you even considered me like this. You were always eyeing up some other girls, talking about this one or that one…” you shrugged, and sat up straight against the headboard.

“I was trying to make you jealous. Guess I was too much of a coward to just be upfront about it,” he paused and swallowed hard. “You were it, though. The one I always thought that would be there in the end.”

“Is that what this is? The end?”

“End of one thing, beginning of another,” he smiled and leaned over to leave a kiss on your shoulder. “Still friends though. That’s always gotta come first because no matter what, you’re stuck with me.”

You felt an odd sense of relief in knowing that this friendship cultivated over two decades would remain and come first. “I can handle that.”

“Good. Now. Can you handle getting your clothes back on? You see, this chick I’m sleeping with distracted me from the burgers on the menu at the bar and I’m starving. She was being a sloppy drunk, I had to get her home–”

You raised your fist like you were going to punch him and he rolled away from you. But your arm hooked around his waist in time to prevent him from getting off the bed. You forced him back to where he was and quickly straddled him again. That look of lust was already back in his eyes as you grabbed his wrists and pinned them back up against the headboard.

“I may have been drunk, but I can still pin your ass down.”

“Unfair advantage when you’re naked and I’m weak-willed.”

You dove down to his neck and left a rough, biting kiss there. “Still want that burger?”

He shook his head and a mischievous gleam glistened in Dean’s eyes. In one swift motion, he had you flipped on your back while he hovered over you and used part of his weight to hold you down. He trailed his mouth down your chest and across your abdomen and positioned himself between your legs. Still sensitive from your first encounter with him, the touch of his tongue against your clit caused a whole body shiver to course through you.

“Fuuck, warn a girl, would ya?” you mewed as your hands gripped each side of his head to try and control him as he lavished your sex with his tongue.

Dean wrapped his arms under your thighs and then pinned them open further, giving him as much access to you as he could get. Your hips moved with him, your moans louder and louder with each pass of his teeth and tongue. This time when you finally came, he refused to let go, drinking you in until your body went limp with exhaustion.

You watched him through the hazy afterglow, sit up and wipe his face clean with the sheet, leaving behind only that triumphant grin.

“Now, I’m ready for that burger,” he winked. “Wanna grab a shower with me real quick? Go find some grub?”

Still, in a daze from everything, you were able to give him a smile and nod, because words just wouldn’t come. Dean helped you up off the bed but held into your hand for a moment.

“Still feel good with all this?” he asked, his features softer than normal.

“Yeah, Dean. More than good. Best I’ve felt in forever, actually.”

“Alright then. Shower, burgers, bed,” he said, picking you up and throwing you over his shoulder as he walked towards the bathroom. Though you playfully smacked at his back to put you down, you never wanted him to let you go. You never wanted to spend another night without him.


End file.
